This invention relates to certain ketals and spirocycles, their agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation.
The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
EP 293,261 discloses heterocycles of Formula i as herbicides: ##STR2## wherein X, X.sup.1 and X.sup.2 are independently O or S;
R.sup.1 is a monocyclic or fused-bicyclic heterocyclic group optionally substituted by one or more groups selected from oxo, mercapto, halo, nitro, cyano, amino, mono- or dialkylamino, amido, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkoxy, aryl, hydroxy, alkoxy, alkoxycarbonyl, alkylcarbonyl, mono- or dialkylcarbamoyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sufonamido, alkylcarbonyloxy, alkylcarbonylamino or heterocyclyl; and PA1 Y is, inter alia, C.sub.2 -C.sub.4 alkylene. PA1 X.sup.1 and X.sup.2 are each independently O, S or N(C.sub.1 -C.sub.3 alkyl); PA1 X.sup.3 is O or S; PA1 each R.sup.3 is independently H or CH.sub.3 ; PA1 R.sup.4 and R.sup.5 are each independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C .sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 haloalkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 haloalkylsulfonyl, halogen, cyano or nitro; PA1 R.sup.6 is OR.sup.11, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 haloalkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 haloalkylsulfonyl, cyano, cyanato, thiocyanato or halogen; PA1 each R.sup.7 is independently C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio or halogen; or when two R.sup.7 are attached to the same carbon atom, then said R.sup.7 pair can be taken together to form --OCH.sub.2 CH.sub.2 O--, --OCH.sub.2 CH.sub.2 CH.sub.2 O--, --SCH.sub.2 CH.sub.2 S-- or --SCH.sub.2 CH.sub.2 CH.sub.2 S--, each group optionally substituted with 1-4 CH.sub.3 ; PA1 R.sup.8 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, formyl, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylaminocarbonyl, C.sub.3 -C.sub.7 dialkylaminocarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl or C.sub.1 -C.sub.6 haloalkylsulfonyl; or R.sup.8 is benzoyl or phenylsulfonyl, each optionally substituted with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 R.sup.9 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; or R.sup.9 is phenyl or benzyl, each optionally substituted on the phenyl ring with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 R.sup.10 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, halogen, cyano or nitro; PA1 R.sup.11 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, formyl, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylaminocarbonyl, C.sub.3 -C.sub.7 dialkylaminocarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl or C.sub.1 -C.sub.6 haloalkylsulfonyl; or R.sup.11 is benzoyl or phenylsulfonyl, each optionally substituted with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 R.sup.12 is C.sub.1 -C.sub.3 alkyl; or R.sup.12 is phenyl optionally substituted with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 X is S(O).sub.n, O or NR.sup.13 ; PA1 R.sup.13 is H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, formyl, C.sub.2 -C.sub.3 alkylcarbonyl, C.sub.2 -C.sub.3 alkoxycarbonyl or C.sub.1 -C.sub.2 alkylsulfonyl; PA1 Y is O; S; NH; N(C.sub.1 -C.sub.3 alkyl); or CH.sub.2 optionally substituted with R.sup.7 when q is other than 0; PA1 Z is a direct bond; O; S(O).sub.z ; NH; N(C.sub.1 -C.sub.3 alkyl); or CH.sub.2 optionally substituted with R.sup.7 when q is other than 0; provided that when Y is O, S, NH or N(C.sub.1 -C.sub.3 alkyl), then Z is a direct bond or CH.sub.2 optionally substituted with R.sup.7 ; PA1 k and m are each independently 0, 1 or 2, provided that the sum of k and m is 0, 1 or 2; PA1 n and p are each independently 0, 1 or 2; PA1 q is 0, 1, 2, 3 or 4; PA1 r is 2, 3 or 4; PA1 s is 2, 3, 4 or 5; PA1 t is 1, 2, 3 or 4; PA1 v is 2 or 3; PA1 w is 2, 3, 4, 5 or 6; PA1 x is 1 or 2; and PA1 z is 0, 1 or 2; PA1 provided that PA1 each R.sup.7 is independently C.sub.1 -C.sub.3 alkyl or halogen; PA1 X is S(O).sub.n ; PA1 Y and Z are independently CH.sub.2 optionally substituted with R.sup.7 ; PA1 k is 0; and PA1 x is 1. PA1 R.sup.1 and R.sup.2 are independently C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio or C.sub.2 -C.sub.6 haloalkylthio; or R.sup.1 and R.sup.2 are taken together to form --X.sup.1 --(CH.sub.2).sub.r --X.sup.2 -- optionally substituted with at least one member selected from 1-6 halogen and 1-6 CH.sub.3 ; or R.sup.1 and R.sup.2 are taken together with the carbon to which they are attached to form C(.dbd.O); PA1 X.sup.1 and X.sup.2 are both O or both S; PA1 m is 1 or 2; and PA1 r is 2 or 3. PA1 R.sup.4 and R.sup.5 are independently H, C.sub.1 -C.sub.3 alkyl or halogen; PA1 R.sup.7 is C.sub.1 -C.sub.3 alkyl; PA1 R.sup.9 is H, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl; PA1 R.sup.10 is H; PA1 n is 2. PA1 R.sup.1 and R.sup.2 are each methoxy; or R.sup.1 and R.sup.2 are taken together to form --X.sup.1 --(CH.sub.2).sub.r --X.sup.2 --; or R.sup.1 and R.sup.2 are taken together with the carbon to which they are attached to form C(.dbd.O); PA1 X.sup.1 and X.sup.2 are O; PA1 R.sup.4 and R.sup.5 are independently H, methyl or halogen; PA1 R.sup.6 is OR.sup.11 ; PA1 R.sup.8 is H or C.sub.1 -C.sub.2 alkylsulfonyl; or R.sup.8 is benzoyl or phenylsulfonyl, each optionally substituted with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; PA1 R.sup.11 is H or C.sub.1 -C.sub.2 alkylsulfonyl; or R.sup.11 is benzoyl or phenylsulfonyl, each optionally substituted with C.sub.1 -C.sub.3 alkyl, halogen, cyano or nitro; and PA1 m is 1; and PA1 r is 2. PA1 R.sup.5 is methyl or halogen and is attached to the phenyl ring position adjacent to the --S(O).sub.n -- moiety. PA1 Q is Q-1. PA1 Q is Q-2. PA1 2-(2,3-dihydrospiro4H-1-benzothiopyran-4,2'-1,3!dioxolan!-6-yl)carbonyl! -1,3-cyclohexanedione S,S-dioxide; PA1 (2,3-dihydrospiro4H-1-benzothiopyran-4,2'-1,3!dioxolan!-6-yl)(1-ethyl-5-h ydroxy-1H-pyrazol-4-yl)methanone S,S-dioxide; PA1 2-(2,3-dihydro-5,8-dimethylspiro4H-1-benzothiopyran-4,2'-1,3!dioxolan!-6 -yl)carbonyl!-1,3-cyclohexanedione S,S-dioxide; PA1 (2,3-dihydro-5,8-dimethylspiro4H-1-benzothiopyran-4,2'-1,3!dioxolan!-6-yl )(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)methanone S,S-dioxide; PA1 6-(1-ethyl-5-hydroxy-1H-pyrazol4-yl)carbonyl!-2,3-dihydro-5,8-dimethyl-4H- 1-benzothiopyran-4-one 1,1-dioxide; PA1 2-(2,3-dihydro-5,8-dimethylspiro4H-1-benzothiopyran-4,2'-1,3!dioxolan!-6 -yl)carbonyl!-1,3-cyclohexanedione; and PA1 (2,3-dihydro-5,8-dimethylspiro4H-1-benzothiopyran-4,2'-1,3!dioxolan!-6-yl )(1-ethyl-5-hydroxy-1H-pyrazol4-yl)methanone.
The ketals and spirocycles of the present invention are not disclosed in this reference.